The leg from Block back into LI Sound (The Gut, Sluiceway or The
Race) was going to be a beat.  The current would start slack and quickly
go foul.  By the time we would be ready to enter LI Sound the current
was sure to be powerfully against us.  Crafting a smart strategic plan
was my challenge.

The shortest route was The Gut, so that was preferred, other things
being equal.  Going the 27 miles from Block to The Gut against an
increasingly foul current would be a challenge.  Other factors were to
try to find stronger wind (we were mostly in 7 - 10 knots of breeze),
and take advantage of wind shifts.  We started the leg on starboard
tack, because that was the slightly favored (lifted) tack.  Our J-44
competitors also left Block on starboard tack and we were chasing them
about two miles behind.

After only about 45 minutes we got a big wind shift, from about 290
degrees to 260.  Our competitors chose to continue on starboard tack,
their strategy was obviously to get close into Montauk Point for relief
from the building foul current.  After a bit of thought (well, a lot,
actually, performed as fast as my tired brain could manage) I
recommended that we take advantage of the header to tack onto port.
This would keep us moving at a much closer angle to the gut than our
competitors.  We would be positioned to take advantage of ANY future
wind shift:  if it went back right, then we would tack back onto
starboard (again heading most directly to the Gut), if more left, then
we would be lifted almost to the mark.

There were two dangers:  if we got no wind shift in the next roughly 3
hours, then we were going into worse current and in slightly the wrong
direction, also, we were getting pretty far from our competition.
After I explained this to Lenny he thought about it for ten seconds,
then simply said, "Prepare to tack".

Half an hour went by, no change in the wind at all.  An hour into this
tack, the wind decreased a bit to 8 knots, but remained at exactly the
same direction.  Half hour more, no change in direction.  I admit I was
getting slightly nervous but showing it wouldn't help at all).
Two hours into this tack, no change in direction.  By this time we were
REALLY needing ANY wind change, otherwise we were in danger of going
through the Race instead of the Gut and it's a disaster to try to go
through the race against a foul current.  The other (better?) option
was to tack onto starboard anyway and take a real beating in terms of
going in a non-optimal direction.

We had about 20 minutes before we reached the race.  With 10 minutes to
go the wind went right five degrees, and I asked for a tack onto
starboard.  Within another five minutes the wind went right another ten
degrees and we were now nicely pointing toward the Gut.  The question
was, what had happened to our opposition?

We sailed through the "lee," current--wise anyway, or Plum Island  This is
the federally owned island where biological (anthrax?) testing is
performed, it's a felony to set foot on the island without a permit.
We tucked up tight under the island, then started heading into the Gut
itself.  Lenny took a look to leeward under the genoa and announced
quite calmly, “Randy, that looks like Brown Eyed Girl".  We were
looking at her bow, she was coming upwind at us, we were clear ahead of
them by an eight of a mile.  It was one of the sweetest sights I had
ever seen.